Hydrochloric Acid → 4-[5-(4-Cyanophenoxy)pentoxy]3-methoxybenzoic acid

HRID 376065Notes

Reaction equation

HRID 376065 reaction equation
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][C:15]=2[O:24][CH3:25])=[CH:5][CH:4]=1)#[N:2].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>O1CCCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]=2[O:24][CH3:25])=[CH:26][CH:27]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723671Tetrabutylammonium HydroxideHCID 18991794Methyl 4-[5-(4-cyanophenoxy)-pentoxy]-3-methoxybenzoate

Product 1

HCID 189917354-[5-(4-Cyanophenoxy)pentoxy]3-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

Methyl 4-[5-(4-cyanophenoxy)-pentoxy]-3-methoxybenzoate (3600 g, 9.74 mol) is dissolved in tetrahydrofuran (36 L) with warming to 30° C. The solution is then cooled to 20° C. and a solution of tetrabutylammonium hydroxide (40% in water, 7.1 L, 1.64 m) is added over 20 minutes. The reaction mixture is then stirred at an internal temperature of 25° C. for 7 hours and overnight at room temperature (23° C.). After cooling to 10° C. with an ice bath, hydrochloric acid (1.0N, 14.4 L) is added over 1 hour. After stirring and cooling to 10° C. for three hours, the product is filtered, washed with water (24 L) and dried in vacuo (76° C., 3 mm Hg) to give 4-[5-(4-cyanophenoxy)pentoxy]-3-methoxybenzoic acid, mp 159°-161° C. HPLC indicates 99.1% purity. A second crop of acid is obtained from the filtrates after diluting further with water (20 L). The product is filtered, washed with water (4×3 L) and dried in vacuo to give 4-[5-(4-cyanophenoxy)pentoxy]-3-methoxybenzoic acid, mp 158°-160° C., (HPLC indicates 98.3% purity).

Workup

  1. temperatureThe solution is then cooled to 20° C.
  2. temperatureAfter cooling to 10° C. with an ice bath
  3. stirringAfter stirring
  4. temperaturecooling to 10° C. for three hours
  5. filtrationthe product is filtered
  6. washwashed with water (24 L)
  7. customdried in vacuo (76° C., 3 mm Hg)

Sources & evidence

ORD record
ord-6bb6ddf1ab9f440687c2c4621ea98478
Source dataset
uspto-grants-1996_01
Patent number
US05488160

Reaction notes

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